Brian Koppelman is a man who’s worn many hats — music executive, screenwriter, and now host of a popular podcast. I talk with Brian about professional trajectories in the modern economy and how having a set career path at the beginning of your career just doesn’t work very well. Instead of having a rigid plan, Brian argues that we should tenaciously follow our curiosity while developing skills that will open up new doors. He gives concrete examples from his own career of how he took this path. We also discuss the importance of hard work, learning to deal with failure and rejections, and what Brian has learned about men, success, and failure from writing movies and interviewing folks on his podcast.

Show Highlights

The advice Brian got from a college professor that changed the way he viewed “career planning”

How to handle rejection, criticism, and setbacks

Why every man should know how to tell a good story

Brian’s writing routine

What Brian has learned about men from writing films like Rounders and Oceans Thirteen

What Brian has learned from interviewing influential people on his podcast, The Moment.

Show Transcript

Brett: Brett McKay here, and welcome to another edition to The Art of Manliness podcast. Well, today on the show we have Brian Koppelman, and Brian is a man of many hats. He started off his career in the music industry, discovered Tracy Chapman. Then he switched over to screenwriting, and he’s written films like Rounders, Solitary Man, Oceans 13, Walking Tall, Runaway Jury, has also produced several other films. Currently, he has podcast on Grantland called The Moment, where he interviews all sorts of different people. Definitely recommend you go check it out.

Today on the show, I brought Brian on. I know a lot of you guys are young guys just starting off your career. There’s this idea and myth that you have to have everything figured out before you start your career. Brian’s a perfect of example of that’s not necessarily the case. The key to a successful career is not knowing every step you’re going to take; it’s acquiring skills that will open up new opportunities to you as they come up that wouldn’t be open to you otherwise if you didn’t have those skills.

We also talk about how to handle setbacks, rejection, failure because he’s faced a lot of it as a screenwriter. We talk about his creative process, his writing process. I know a lot of you are creative types. We talk about what he does to get the muses, or get the creative juices flowing.

Then we also talk about what he’s learned about being a man from writing films. I’m always interested in, and looking, analyzing films, and what we can take away from them on what it means to be a man. It’s just a really fascinating discussion. I think you’re going to enjoy this. Let’s get on with the show.

Brian Koppelman, welcome to the show.

Brian: Oh man, Brett, it’s my pleasure to be here. I love listening to your show, so it’s great to get to talk to you.

Brett: Thanks, man. Let’s start off with this question. You have one of the most varied work backgrounds I’ve ever seen, and I’d like to use this as a starting off point for our younger listeners. One thing we try to hit on, on this site when we talked about your career is that you don’t have to have things figured out when you’re 20 years old. There’s no straight path to the career that you want.

Can you walk us through your background? How you went from music producing, to film, and screenwriting, and podcasting. Tell us what happened.

Brian: Sure. I mean I even think, of course I’m happy to do that, but I even think that the specifics, and I will do that. I’m not going to not do that. I’m happy to walk through any of the specifics, but the global thing that I picked up, and not only in hindsight now looking back, even as I was going through those things, I had a professor in college, this guy’s name is Sol Gittleman. I went to Tufts in Boston. He looked us one day in class, and he said, “I just want you guys to know that before you’re 30, people live longer now. People have a different kind of existence. There’s this idea that you’re going to coming out of college, know exactly what you’re going to do, pursue that thing, and stay at that job forever, that career, that industry. You guys are walking into a different world. Don’t panic if you switch three times before you’re 30 years old. If you do, I think that just shows that you’re curious, engaged, interested, and not settling. Remember, I told you this here when your parents, friends, significant other, are worried that I said, if you keep chasing things for the right reasons, you’ll land okay.”

I will tell you that that’s not the only thing that was sort of like a beacon, but the idea that I wasn’t bound by assumptions that I had yesterday, or a year ago, but that I could take in new information, grow, and make new assumptions, and that if I kept doing that, if I kept being welling to be uncomfortable and take those risks, and follow my curiosity. People talk about whether you should follow your passion or not, but for me I frame it slightly differently. I talk about curiosity. Yes, passion. Obsession. If I would keep following the things that I really cared about, and then I worked as hard as I could to get closer to that direction, I was like, that’ll get me to a better place.

That started when I was 19, and I was at college, then went into the music business. I had family connections to the music business. My dad was in the music business, so I knew about that business.

When I found a recording artist who ended up becoming very successful, and I discovered her, it seemed like that’s what I was going to do, but I was immediately, well, not immediately, fairly soon realized I didn’t want to be an executive in any business, even a business that seemed glamorous. That particular path wasn’t for me, to be somebody shepherding artists.

I went to law school at night because I thought I wanted to be a civil rights lawyer. I wanted a better education, so I did that at night because I felt like I needed that body of knowledge. I needed to continue to grow my mind. I thought I’m going to do this and go at night.

When I was doing that, and really started doing work to figure out who I wanted to be, I realized maybe that wasn’t the answer. Around that time, a little later, when my first child was born, that’s when it really crystallized for me, that I wanted to be the kind of person who could come home and tell his kids to do whatever they wanted to be. If I wasn’t going to face whatever I was really scared of doing, and I really wanted to do, I wouldn’t be able to be that kind of father. That’s when I realized I want to make movies. I’ve got to figure out how to do that. I have to figure out how to live as a creative person. That’s when I then really started making a concerted effort on a daily basis to do that.

I’ve followed that pattern ever since. Since then, I haven’t abandoned anything, I’ve just added to it. I’ve used that same approach to attack any field of endeavor in which I was really interested.

Brett: I’m curious. Did you finish law school? Because I went to law school too.

Brian: Yeah, I finished, man.

Brett: Okay, yeah. I finished. I started the blog while I was in law school, and then it took off. By the time I graduated, I’m like, I’m not going to practice law. I’ll just do this.”

Brian: Me too. I knew it, I was playing poker by then too. My wife got pregnant during, right at the last year of law school at night. Amy got pregnant, and we started talking about some of this stuff. Then when our first son was born, our first child was born, I’ve got a son and a daughter, it truly was clarifying.

Since then, I’ve thought about all of this a lot. I’m so lucky that I had a supportive wife who really is the person closest to me and always has been, and who said to me, “I agree with you. There’s more here. Go and chase this thing.” I didn’t quit my job through any of that stuff. I didn’t abandon my responsibilities. You had a guest on a few months ago. What’s his name, Cal?

Brett: Cal Newport.

Brian: Who’s great, a really bright guy. He talks about the pitfalls of following your passion. I understand where he’s coming from. I understand that when you’re move is safe that it can put you in a powerless position. You chase this thing, it doesn’t go well. I understand all that stuff rationally. I’m more in the camp of somebody like Jon Acuff or Tony Robbins, who talks about there is a way that you can, not in an irresponsible, irrational crazy way, but in a concerted, effortful way, you can chase down the thing that you believe you have to do, without giving up on the things that are your responsibilities that you owe, that you need to do to protect yourself and those that you love.

I just would work extra hard. I would get up extra early in the morning. My best friend, other than my wife, is this guy, David Levine. We’ve been like brothers since we were kids. We wrote Rounders together by meeting two hours every single morning. He would finish bartending. I would get up early before I would start my work day, and we met every day, two hours a day, until we finished that script. We never missed a day, and neither of us ever flaked on the other guy. We did the thing, showed up and did the work. Then I’d go on and do the work of the job that I was paid to do.

I do think that taking these kind of incremental but determined steps, following your passion. I think if it’s not your passion, it’s very hard to do that, much harder. If it’s not your passion, if not something you believe in, if it’s not your calling, it’s much harder, I think, to put in the sort of super effort that’s required to make a gigantic change, or to take yourself all the way to the next level.

I think that an unintended negative consequence of not taking those chances is, and this is a core belief that I have, which is that if you allow yourself to be blocked, if you don’t access that most creative part of yourself when you hear the calling to do it, if you do, I think you start to become toxic. Self-loathing shows up. Then I think, unwittingly, you take that out on those that you care about. It starts a really bad cycle of heading towards a place of darkness and depression.

I think the moment that you realize you can chase something, you can believe in yourself, as long as you’re willing to do really hard work to get there, then I have found through the life I’ve been living, that the possibilities are kind of limitless. Anyway, that’s, I know, a very optimistic way to look at the world. I don’t want to sugar coat it. There were lots of times that it was really scary, and it seemed like a failure was imminent, but I‘ll tell you it always feels that way, right? Anytime you take a big creative risk.

When I launched my podcast, one of the reasons I did it was I knew something in me was frightened of really putting myself forward in that way, but I really wanted to do it. I really wanted to have those conversations. I really wanted to engage with people I admired in a very specific conversational pursuit. But I was scared.

I have a really good life in so many ways, and I was putting myself out there on Grantland which was a big platform right away. I could have really opened myself up to derision and mockery. I was just like, “No. I have to put my money where my mouth is. This is the stuff I tell people. I have to do it too.”

I’ve been so rewarded for having done that, in so many different ways, just by the people that I’ve met doing it, and through doing it. I found that each step of the way. The same thing about making movies. I get to work with and be around all these creatively inspired and inspiring people. That just charges my own creativity and lights me up.

You asked me to talk to younger guys listening, whatever the thing is that you know lights you up, whoever the people are doing that, I think you owe it to yourself to find to a way to start bouncing off of those people.

Brett: Yeah, I love your approach. That’s the approach that I took. People always ask me. It’s like, “I want to do what you do. Did you just risk it all and just delve right into it?” They always say, “You’re such a risk taker.” I’m like, “Honestly, I’m one of the least risk adverse people.” I’m very conservative in a lot of ways when it comes to risk.

I took that approach, where I did this on the side. The Art of Manliness started off as a side hustle. I got up extra early in the morning, worked two or three hours on it, went to law school, put in a full day of work there. Then I worked on it late into the night. I didn’t make the actual leap until I was pretty sure that I could support my family with this, and then I made it.

I did have that itch, that creative itch there, and I scratched it. I just had to work extra hard. That’s always my advice to people. It’s like you don’t have to jump whole hog into it. You can still be creative and take that entrepreneurial risk, whatever it is, while still maintaining your responsibilities to yourself and to your family. Your approach is my approach. I love it.

Brian: Yeah, I was going to say I really agree. There’s a great book on that. My buddy, Jon Acuff, he has a new book coming out in April call Do Over. You have to have him on the show. That book’s going to be number one bestseller. He’s written two number one bestsellers, but that book is far and away his best one. It really talks about this kind of career flip.

He’s written a book called Quitter and a book called Start. Even though Start is the newer one, I would really suggest people look at this book, Quitter. It’s definitely a challenging title, the name of Quitter. It’s a controversial title.

It’s about how to put yourself in a position that when you finally quit and make the change, you’re ready to do it. You’re prepared. It codifies this thing we’re talking about. I’ve told Jon, I wished that I’d had that book when I was having to figure this stuff out for myself.

Brett: You’re a successful filmmaker, did screenplays for a lot of very great films. I know the process of actually getting there is just bereft of rejection after rejection after rejection.

How do you handle that as writer? Where it’s just like, you submit something, and they’re just like, “No, I don’t like that.” What do you do psychologically to handle rejection? Even our listeners who aren’t writing screenplays, they’re going to face rejection in their life, some form or shape. How do you fortress or girdle yourself up, psychologically, to handle that?

Brian: It’s a great great question. Look, I do these Vines, as you know, this Six-Second Screenwriting Vine series that ended up turning into a … One of these Vines has almost 40 million loops. The last one I did, the most recent one, I talked about rejection. I said nobody likes rejection. It’s like nobody likes getting stung by a bee. It hurts. But you have to just make yourself sort of immune to feeling it. You have to just know, hey, it’s a bee sting. It hurts. I’ll be better tomorrow, and I’ll keep moving forward. The bee sting is not putting me in the hospital; it’s not knocking me out.

I’d say this. Rejection is different than critical feedback, but I do think that in both things you can go through a process, or I try to go through a process, which is I try to wait to grapple with it until I can look at it dispassionately. If I can just look at it for a second and decide if there’s merit in it, or if there’s not, if there’s something useful I can take from this rejection. Is this rejection just that somebody didn’t get it? Or does this rejection have to do with something fundamental?

I don’t want to look at that emotionally. It may mean I have to look at that a week later. I have to somehow process and move on, and then go back to it. Essentially, I learned at a very young age that experts almost are very, very often wrong. Gatekeepers are paid to say no because no saves money in the short term, but saying yes is the thing that puts their jobs in immediate jeopardy.

If you understand that in all aspects, they’re rewarded short term immediately, for safe guarding against loss, then you know it’s not really a value judgment on you, and who you are, and what you are. You understand that it has to do with what their pressures are, what their lives are.

The recording artist, the singer/songwriter I found when I was in college, was this woman named Tracy Chapman. I worked with Tracy, and made her demos, and made her first album with her. She made the album. I helped her make it. She was rejected. I would take her demo tapes around to all the record companies, and they all rejected it for one reason or another. The album sold over 10 million copies worldwide when we finally broke through.

Then Rounders was rejected. I’ve told this before, but for your audience, Rounders was rejected, that screenplay, was rejected by every agency in Hollywood, CAA, William Morris, ICM, UTA, all the famous agencies. They all rejected the script. Then when Miramax bought the movie, bought the screenplay, the next day, every single one of them called us and tried to sign us. I said to them, I read them, because it was my first one, I wrote a bunch of stuff down, so I would read them, why they rejected the script, and they were going, “No, that wasn’t me. That was my assistant.” Or some reader, a million excuses.

Through those experiences, and when David and I produced the movie The Illusionist, at every step of the way, that got rejected too, I just learned from those experiences that, yes, it stings. Honestly, they don’t really know. They may know. It doesn’t mean that they never know, but what it means is that because no is the easiest thing for them to say, because no is the reflex, you have to really fight and be committed in order to get that yes.

You have to know that you’re not a failure. You’re not worthless. All that happened is a business person made a business judgment. In all likelihood, they’re going to make many business judgments that are faulty, and it’s very easy to slot yours into that category.

That’s how I look at it. Again, it doesn’t mean it’s never emotionally painful in the immediate moment, but it does mean that I’m comfortable facing it. It does mean I’m comfortable saying, “I’m going to take these next how ever many months and write something on spec.” As opposed to, where you get to a place in this business where, in my career we have a track record, Dave and I could go pitch stuff, and pitching is, if you’re comfortable in the room with people, and you know how to talk, and you have a track record, pitching, you can get an answer very quickly. Most of the time, you’re going to get a yes. They’re going to pay you to write the thing.

But if you spec something, in other words, if you take the risk of writing it without a buyer in advance, you have much more control over what happens to the material if they want it. Of course, the risk is you put in all this time, and they don’t want it.

I’ve gotten to a place where I’m very comfortable taking that risk. The show that I’m making right now for Showtime, which is called Billions, and I’m shooting starting in January 19th in New York, stars Paul Giamatti and Damian Lewis from Homeland. That’s a screenplay that my partner, Dave, and our friend, Andrew Ross Sorkin, who’s a great writer about finance, he wrote the book, Too Big To Fail. Dave and I and Sorkin wrote this thing on spec, and knew we could get money in advance for it from any of the cable networks.

Instead, we said, “You know what? Let’s take this risk because then we can say to whoever wants to buy it, ‘Well, if you were to buy this, you have to guarantee us you’re going to at least shoot the pilot.'” Which is a huge investment of many millions of dollars. Not to us, but to making the show.

The only way to get them to do that, the only way to switch the leverage is to take a risk and to create something that they’re going to want. The big risk is I take four months of my life or three months of my life, and they don’t want it. Then I’ve wasted that time. I didn’t earn money during that time. I also have to deal with the sting of the no.

I’ve gotten very comfortable with that because the rewards of it are so great. I can handle the little bumps in the road or losses along the way. I’ve trained myself to be a fighter, the way a fighter trains himself to take a stiff jab. You watch a fighter take a stiff jab, and we’re so used to it now, in MMA especially. You watch someone land on somebody. A shin kick, let’s say, in MMA. A guy kicks another guy in the shins, and a guy blocks it. We watch them do it, and they take those shots like they’re nothing, but the first time they walked in there, you know that that shot to the shin was crippling.

You know what they do, because I know you had Sam Sheridan on a long time ago, a couple of times, you read that amazing thing in Sam Sheridan’s book when he talks about how they make their shins really tough. They keep brushing them, and rubbing them, and hurting them, and crushing them. That’s the process, man. You’ve got to learn to love that particular kind of pain.

Brett: Yeah, you’ve got to become mentally callused in a way.

Brian: You do, right?

Brett: Yeah.

Brian: In order to keep growing.

Brett: All right. You mentioned your Vine, where you dispense screenwriting advice, or just writing advice in general. I often think that unfortunately storytelling is often just, the importance of it, it’s relegated to what you do, or what I do, like writers, or screenwriters, or film. But do you think it’s important for people who aren’t in that business to know how to tell a good story? If so, what are the big checkpoints of telling a good story?

Brian: When you say is it important for them to be able to tell a good story, do you mean to be able to tell a good story verbally, or to be able to write a good story?

Brett: To write, to be able to fashion a good story, whether it’s verbally. I can see storytelling, like pitching, you’re telling stories, whenever you’re writing a memo.

Brian: Yes. It’s an incredibly useful skill to have, for sure. But I think that it’s an innate skill, the ability. We all communicate through the use of story. We can all get any of your friends, to tell you the time they were the most embarrassed by a girl in high school. The most embarrassing moment they had with a girl in high school, whether that means they were in a movie theater, and another friend of theirs saw when they were trying … They could tell you the story, and in a way that would make you laugh and be engaged.

The reason they can do that is that that moment was heightened for them, so that they remember it, but it’s also that they’re very comfortable around you. You put them in a state where they’re comfortable. They could tell you that story, and it’s compelling, and funny, and engaging, but if you put them on stage, maybe it’d be scary.

To me, it’s all just about finding the authentic self because the more you’re comfortable in your own skin, the more you’re comfortable being who and what you are, the more natural and easily you can tell a story. I wouldn’t even encourage people to think of it as storytelling. Think of it as just communicating, and becoming just more and more comfortable being around people, and being around yourself.

The more you’re pursuing the thing that dovetails, that strikes the chord inside of you, then the easier it is. You’re closer to being yourself. The closer you are to that, the more people pick up on that. They see your confidence. They’re engaged by you. They read that as charisma. Then, suddenly, your storytelling is that much better. Does that make sense?

Brett: That makes sense. It makes perfect sense.

One question I was meaning to ask you about when we were talking about your career, we’ve talked about how you’ve done all these different things. Do you think there’s some unifying skill or skill set that you developed or acquired throughout all these things you’ve done? What would you say would be the unifying thing that connects?

Brian: It’s a great question. I think it’s being able to recognize the things that are going to keep my interest, what I’m curious about. As a kid, I was a high IQ kid who was not a great performer in school. At the time I was in school, people didn’t recognize what ADHD was. There was no treatment for that. They would read that as laziness, or as obnoxiousness, or as disinterest.

Kids who were undiagnosed ADD, in my generation, I think it was really hard in certain ways to hold onto a sense of self. It’s very important for me. I had parents who encouraged me, and who didn’t doubt my ability and my intellect, despite doing poorly sometimes in school.

I started, even when I was young, 13 years old, 14 years old, when I would want to say, “Hey, I want to start managing bands,” or, “I’m going to go to this night club, and I’m going to say, hey, can I have your club on Saturday afternoons? I want to put teenage bands, playing for teenage audiences.” Or, “Hey, there’s a guy doing something in California about heavy metal guitar players. I know a heavy metal guitar player. I’m going to get them together and take a piece of it.”

They encouraged it because they saw that I was following this curiosity, enthusiasm. When I was engaged, I would be able to really work hard, and perform and get good results. I just think that’s the single thing for me.

By the way, luckily for me, reading. Even though the way the ADHD would manifest itself for me was if I had to read a dry history book, it would be like the book was radioactive. I could not do it. There was nothing that could get me to read that book, but I always loved novels. I loved great non-fiction, biographies.

I would read, and read, and read, and read, and I would even take books into when I was supposed to be doing something else in school, I would just be in the back reading all the time.

That’s just a lucky thing. I just happened to really love to read, and reading, of course, unlocks everything else for everybody. I loved that, and that would stoke my curiosity, and that would give me a road map of what I wanted to go after and chase.

I ended up going to a very good college. I was of a generation where no one knew you were supposed to have all these extra curriculars. It didn’t matter. It wasn’t something we thought about, but it just so happened I did all this stuff that made me far more interesting to a school than someone who got way better grades than I did, but didn’t do anything with their lives.

Brett: Yeah.

Brian: I think I probably just followed that model the whole way.

Brett: Hey, I loved the bit about, it sounds like great parenting advice, what your parents did with you. Encourage your kids to follow those curiosities. It reminds me a lot of … We’re big fans of Teddy Roosevelt on The Art of Manliness. I don’t know if you’ve seen that.

Brian: Me, too, man. I’ve just been reading the book about when he was in the … I’m just blanking on the name of it. I’ve just been reading it, the one he wrote about when he was in the military.

Brett: There was this one biographer who said about Teddy Roosevelt, if ADHD existed back in the 1890s, they would have diagnosed Teddy Roosevelt with ADHD because he was that kind of kid. I’m interested in natural history, so he would go shoot birds and stuff them, or he’d write a book. She said if he was alive today, they would put him on Adderall, and there wouldn’t be a Teddy Roosevelt.

Brian: Right. Yeah, it’s hard for me to tell. I’ve taken Adderall at different times in my life. I don’t demonize those things. I think that they can be useful. I’ve often wondered if I would have had that, as a child, whether … There’s no way to go back in time.

Brett: Yeah, you never know.

Brian: Would it have helped the painfulness of sitting in those classes and not being able to connect? Do you know what I mean?

Brett: Yeah.

Brian: There’s no way to know. I agree that it’s crazy how over-prescribed those medicines are. My instinct is like yours, which is to say I think in the end, if you can get there without ever doing it, but have to see what it’s like under medical supervision taking it.

I do understand it’s the way that you know you have ADHD is that under doctor supervision, when you’re a grown-up and you and you go, “What was going on me?” And they go, “Here, take this medicine, and try this.” Suddenly, you do see the way other people can get through the world. It is a fascinating thing to see, I’ll tell you that.

Brett: What was the difference? I’m curious. Just what did you notice?

Brian: The way in which things that would have before utterly, the way in which I couldn’t focus on stuff other than if I was really, really interested in it, I could focus on it. I could sit and just complete tasks in a much more consistent manner. For somebody who can’t do those things, it’s a really big difference.

By the way, as a grown-up, of course I compensated in all sorts of different ways, figured a lot of that stuff out. Listen, if I could have read the boring history book, I would have gotten all As in history. Instead, I wouldn’t read the book, I would show up a half-hour before, talk to people, hear what they had read, and still pass everything.

I wonder that. There’s no way I can know. There’s no way I can go back. For sure, in the end, what anyone I would talk to would say is that I probably would have just then been like a success, some kind of a lawyer in the courtroom. I wouldn’t have done any of this creative stuff. It’s hard to tell.

Brett: You never know.

Brian: I do think, in the end, it was a big blessing also. Obviously, it led me. It probably is what made me an artist. Otherwise, I probably would have never become an artist. I wouldn’t have had to.

Brett: All right. You mentioned a little bit your approach to writing, when you talked about when you wrote Rounders with your writing partner. I’m curious. What is your approach to writing? It sounds like you have a very workman like approach to it.

Brian: Yes, well.

Brett: Do you believe in inspiration? Or are you sort of like Jack London, where you sort of like beat it with a club?

Brian: It’s got to show up. You’ve got to show up. When you’re young sometimes, you can get away with, I’m going to chase inspiration at two in the morning, and when it shows up, I’ll stop everything, and I’ll write like in the Charles Bukowski fever dream. I don’t know if you’ve seen the film Barfly with Mickey Rourke which is about one of these wandering peripatetic poets. Charles Bukowski. It’s a really fascinating, dark twisted movie.

You’ve got to show up every day. I show up every day. Right now, I’m in production, I’m only writing, working on Billions, and fixing that other than blog posts or whatever, other little bits of writing because I’m casting and locating scouting and putting together the show. We start shooting. That’s one of the great rewards of doing what I do is that I get to do this little thing with Dave when we’re in a room writing, and then suddenly I’m running this thing, Dave and I running this thing, where there’s 110 people all working together to bring this vision to life.

When we’re writing, every day, 9 AM in the office. I walk in the morning. My creative practice is pretty locked in. I get up. I meditate. I practice transcendental meditation. I meditate for 20 minutes, then I do morning pages. I do the three longhand pages. Then I take a long walk. I’ll walk my daughter to school, and then I will take a long walk a couple of miles to my office. I get up really early, so I’m still in my office by 9, sometimes before 9.

Then Dave and I meet. We’re probably bullshit around for half an hour, and then we start in. We just start writing. We’ve made a plan. We know what we’re doing. We know what we’re doing from the day before. We know where the thing is going. Some days it’s really difficult because writing is hard. Story is challenging. Sometimes it’s easier.

It’s not going well, sometimes it’s because, Bri, you flaked out, and you haven’t done morning pages in three days. I’ll make sure I get up. Time got away from you, so I’ll make sure to get up even earlier for the next week to make sure I don’t miss doing morning pages. That, for me, is the thing that always starts the creative process going.

I’ve been stuck. When I was writing Solitary Man which Dave and I directed together, but I wrote myself, I was really stuck in the middle of it, and I couldn’t figure out why. I knew I was scared of something. I couldn’t find the answer. I couldn’t find the answer. I realized, I don’t know what the connection is to this, and the movie’s not a comedy, but I decided, I realized in doing morning pages, thinking that I always wanted to do standup. I’d never really done it. It was one of the only things I was truly frightened of.

I did standup for a year-and-a-half. I did four nights a week in Manhattan. I started with open mics. I ended up getting to be able to perform at a bunch of the clubs in the city, actual real gigs. Somehow in that process something snapped, and I was able to find the answer and finish writing Solitary Man.

I’ll do whatever I have to do. I’ll chase down whatever I have to chase down in order to unlock this thing that’s most creative in me, but I also do show up every day to do the work. I don’t know. If you don’t, it’s too easy to not do it, and then tell yourself this story that you’re not really a writer. You’re not really an artist. You’re not really a creative person. You’re a fraud. Ultimately, all that stuff is connected to this worry that Tony Robbins says that you’re not good enough, or that you’re really in the end, if they saw what you really were, they would think you were a fraud or a fake.

That’s one of the things I tell myself. Like on a day that I’m not in the mood to meditate or I’m not in the mood to do the morning pages, it’s easy. It’s one of the things I love about speaking. I tell people I do it every day, so if I don’t do it, I’m a fraud. I’m a liar. I’m like, are you a liar? No, you’re not a liar. Good. Do the morning pages. That’s proof that you’re not a liar.

Show up at your office at your desk and write something. If you don’t, you’re no better than those guys out there bullshitting people. If you do, you’re telling the truth. I’m there, doing it every day. It’s how I approach my whole life.

Brett: What are morning pages? What is that exactly?

Brian: It comes out of Julia Cameron’s book, The Artist’s Way. I will say there are things in that book that I don’t love. The book has a lot to do with spirituality. I’m an atheist, but she came up with this idea that if you wrote three longhand pages every day, in the morning, free writing as like the first thing you did during that the day, that it would cure a lot of people’s writer’s block.

She’d done a bunch of studies with this at a bunch of seminars, and found that it solves many of the reasons people are blocked. The largest reason is people are perfectionists, and they’re scared that what if what they do is not good enough. The point of morning pages is, you just keep your pen moving. It has to be longhand, for three pages. You don’t stop writing. You fill these three pages.

What happens when you do it every day is first, you’re like neurosis and anxiety gets out on the page. If there are things that you don’t like about what’s going on, but what happens is you’ve now wet the wick. You’ve lit the wick. You’ve now started priming the pump, whatever the metaphor is, but you’ve started to get the creative juices flowing in a very free way.

There are a bunch of rules about the morning pages. One is you’re not allowed to read what you write for five years. Nobody else can read it. It’s not for publication. It’s literally to get the shit that’s in your head out. You do these three pages.

The people that I know that have actually read Cameron’s book, and then have done the pages, who have actually done this for three months, the percentage of those people who have written books that have gotten published, or have written movies that have gotten made, is staggeringly high.

That’s what that is, morning pages. That three longhand, free writing pages. I did that. A big part of when I shifted my life when I was that age, when I had my son, when my son was born, I did read two books right then. I read Awaken the Giant Within, and I read The Artist’s Way. Those two things together helped me figure out what my exact attack to doing this was going to be.

Brett: Very cool. I like that. I like that practice. I’m going to start doing that. That will help me out a lot. You’ve made a lot of great movies. You mentioned a few of them, The Illusionist, Rounders, Solitary Man. You also did Oceans 13.

I’m curious because I run a blog called the Art of Manliness. Everything I do is colored through the lens of looking at it, is this manly? What can learn about being a man from this?

Brian: That’s funny.

Brett: I’m curious. Are there any insights that you’ve gleaned from your work on your films about masculinity or manliness? I’m talking about both the good and the bad. Or do you even think about it at all?

Brian: It’s interesting. I learn more of that all about by being a parent. I think I was very focused on that stuff, like the movies that I would watch, Diner, or the David Mamet movies, or The Godfather movies, those things that made me want to do this, or that put this in my head, and that I would watch over and over again, certainly gave me certain ideas of about what it means to be a man. In a way, the most manly thing is to know that it’s all really about what it means to be a human, and what it means to be a caring person, and a giving person, and how you hold on to this idea of manhood while being soft sometimes and giving.

There are a couple of different archives of the writer, and yeah, Hemingway is like that old-fashioned kind of like masculine, tough thing, but I think that that’s an outmoded idea of manliness in a way. Listen, the most manly human being I’ve ever heard in my life, I think, is that guy you had on a few weeks ago that won the Congressional Medal of Honor. Sorry, not won it. Sorry, he was presented with, by his language. When he was presented with the Congressional Medal of Honor, Paul … What’s his last name?

Brett: He’s Polish. Bucha.

Brian: Right. Paul Bucha. Hearing his story, and the way that he downplayed the events of that night. Then you go and look up the events of that night afterwards, and he did a lot more than he said that he did that night.

If you really think about what he was, if you really process it, that guy that night was the most giving human being in the world. He was tough. He was courageous. These are ideas that we associate with manliness, but what he really was, was self-sacrificing and giving to those men on the battlefield that he cared so much about.

I was so moved by that. I called my son, who I never want to go into the military. He’s 18 and at college. I was like, you’ve got to listen to this because there’s an ideal presented in here about what it really means to love your fellow man in a very specific way that I think is about duty and honor and obligation to hold to these ideals. It really just blew me away.

Yeah, I think about these things, but I think I look at it from a little of the other side now.

Brett: Got you. That’s really great stuff. Yeah, his story was fantastic. I’ve talked to other military guys, and most of them are very similar to Paul. They’re the humblest, and they just talk about, they just focus about their platoon, or their group that they were with, and just like how much they loved. They say it. I loved those guys.

Brian: Yeah, and I think it’s about the mutual sacrifice. The thing in that episode of your show that was so amazing to me is he saved all those guys, but 10 guys got killed, and you could feel the cost of losing those 10 guys, even though it was so obviously not his fault. It was so great. The pain of that was so alive, but he also would not indulge that. Like he wouldn’t indulge in, feel sorry for me because I lost those guys. He was just in every way to me the embodiment of somebody living up to their best idea of themselves.

Maybe that’s the ultimate manly thing to do is to have really ambitious idea of the possibility of yourself, and then your try your hardest to live up to that.

Brett: Yeah, that’s a very ancient Greek idea. The idea of being a man is having a life of eudaimonia, or a flourishing life, and striving for this ideal. You might not achieve it, but there’s growth in the striving. There’s something in the striving.

Brian: Sure. It ties into what Ryan Holiday always talks about. His last book was about the Stoics.

Brett: Yeah.

Brian: Handling the setbacks and choosing to see them as opportunities to perfect this ideal self that you’re trying to get to.

Brett: You mentioned your podcast. It’s interesting because it’s a podcast with, you have entrepreneurs, artists, but it’s on Grantland. I typically associate Grantland with sports and some fantastic sports writing, some of the best I’ve seen in recent years. What’s your goal with your podcast on Grantland? What are you trying to do with that?

Brian: I ended up on Grantland because Dave and I directed a 30 for 30 on the tennis player, Jimmy Connors. When we were promoting that 30 for 30, which I’ve got to say, Rolling Stone just said it was the fifth-best 30 for 30 of all times.

In doing it, when I was promoting that 30 to 30, I went on the B.S. Report with Simmons. Before that, I’d been Jay Mohr’s podcast a couple of times, and had done some other ones, then I started doing those Vines, and I realized that I wanted to communicate in this way. I was talking to Seth Godin, who is a mentor to me in certain ways, a friend, and gives me great counsel, and Seth and I was talking about it. He was like, you know, do this podcast. Go ahead and chase it if you want to. I wanted to, so I said I’m going to do it.

I called Simmons because I know Simmons, and I said I’m thinking about doing this. I knew I could do it somewhere else, but I was loyal to Grantland. I had written for them from the beginning. I really like Bill. I thought, before we were talking about it, I thought they wouldn’t want me to do it there, but he was like, “Do it. Give it a shot. Let’s see if it makes sense.”

I talked to Jacoby, figured out that I wanted to center it on, it’s called The Moment with Brian Koppelman, and the central concept of the podcast is that people who accomplish remarkable things process the high and low moments of their lives, the inflection points, differently than we do. They use those moments for fuel. That’s what I was interested in talking about.

Currently, it does have a big pop culture presence. As a result of that, I started to hook up with them. I got immediate feedback that people were interested in this conversation. Seth Meyers was my first guest. Mario Batali was my second one. Right away, you’ll have seen that there was a big difference between who those people were. Early on, I had Baron Davis on. I had Marc Maron on. The last few weeks, I’ve had Marcus Lemonis from The Profit. I had Killer Mike from Run the Jewels. I’ve had poker player, Phil Hellmuth.

It does run the gamut, but my one rule of the show is I won’t put anybody on the show who doesn’t fascinate me. I can do a really great job interviewing someone if I’m really engaged and interested, the same thing, all across the board. If I’m interested, than I can go dive into the research. I have things that I’ve been thinking about for a long time about them. I can try to bring something out.

I have to say it’s been incredibly satisfying. The one that I did with Killer Mike, who’s this incredible 39-year-old rapper, who is finally becoming a star even though he’s made great music for a long time, we come from such different places. It’s so unlikely in a way that he and I would be friendly with one another, but we’ve had an internet friendship for years. He happened to perform in Ferguson the night the grand jury decision came. He was the only person. His band, Run the Jewels, he and this guy, El-P, they were the only people not to cancel a show that night.

He made this incredible speech that you should see on YouTube before he performed, and he and I spoke a week later when he was playing a sold-out gig in New York. The way that people across all economic lines, racial lines, have responded to that show in that particular, the letters I’ve gotten, the things people have said to Mike, it’s like it is the most rewarding thing. I know you get it from doing your show. It’s so rewarding to be engaging in this big conversation now that’s made possible by Twitter and by podcasts. It’s not just a conversation with Mike. I’m talking to thousands. I’m engaging with thousands of people about this stuff that we’re all really interested in. I’m just so happy to have the platform to do it.

Brett: That’s great. Where can people find more about your work? Besides Billions, do you have any future things planned?

Brian: Yeah, I always have stuff planned. Dave and I produced a movie that my wife wrote, based on one of her novels. She’s a novelist, and it’s called I Smile Back, starring Sarah Silverman. It just got accepted into the competition at the Sundance Film Festival, which is a really big deal, like 1.5% of the movies that try to get into Sundance get in. Huge, big deal that that film’s in Sundance. It will come out next year.

Billions is taking up a lot of my time. Then there’s The Moment. If people want to reach me, they can find me on Twitter, @BrianKoppelman. I also give out my email address which is [email protected]. I’m happy to hear from you about anything, but if you send me a screenplay or a screenplay idea, or a TV show idea, do not do that. If you do that, Brett is going to find the seven most manly guys he knows, and they’re going to track you down.

Brett: Thank you. Our guest today was Brian Koppelman. He is a screenwriter and the host of the podcast, The Moment with Brian Koppelman. You can find that on iTunes. Also, just Google The Moment with Brian Koppelman. You’ll find it there as well. Definitely recommend that you go check it out.

That wraps up another edition of the Art of Manliness podcast. For more manly tips and advice, make sure to check out the Art of Manliness website at ArtofManliness.com. I’d really appreciate it if you would go check out our store. It’s Store.ArtofManliness.com. You can find all sorts of Art of Manliness products.

We’ve got a really cool virtue journal that we developed, one-of-a-kind, unique. You can’t find this anywhere else. It’s inspired by Ben Franklin’s diary. It comes in a nice leather case, so go check that out. Great thing to use and start off the beginning of the year to track your progress in become a better man. That’s Shop.ArtofManliness.com. Until next time, this is Brett McKay, telling you stay manly.